有机化学 ›› 2014, Vol. 34 ›› Issue (11): 2296-2303.DOI: 10.6023/cjoc201404043 上一篇    下一篇

研究论文

N-取代苯甲酰-N'-(5-甲氧基-2-甲硫基嘧啶-4-胺基)(硫)脲的设计、合成及生物活性研究

李成坤a, 姜林a, 王悦a, 万福贤a, 张沛之a, 李映a, 崔紫宁b   

  1. a 山东农业大学化学与材料科学学院 泰安 271018;
    b 华南农业大学资源环境学院 广州 510642
  • 收稿日期:2014-04-24 修回日期:2014-05-20 出版日期:2014-11-25 发布日期:2014-07-02
  • 通讯作者: 李映,ly8049@sdau.edu.cn;崔紫宁,ziningcui@scau.edu.cn E-mail:ly8049@sdau.edu.cn;ziningcui@scau.edu.cn
  • 基金资助:

    山东省中青年科学家科研奖励基金(No.BS2011NY013)、山东农业大学青年创新基金(No.23682)、国家自然科学基金(No.21102173)、山东省科技发展计划(No.2013GZX20109)和华南农业大学校长科学基金(No.4200-K13014)资助项目.

Design, Synthesis and Biological Activities of N-(Substitutedbenzoyl)-N'-(5-methoxyl-2-methylsulfanylpyrimidin-4-amino)(thio) Ureas

Li Chengkuna, Jiang Lina, Wang Yuea, Wan Fuxiana, Zhang Peizhia, Li Yinga, Cui Ziningb   

  1. a College of Chemistry and Material Science, Shandong Agricultural University, Taian 271018;
    b South China Agricultural University, Guangzhou 510642
  • Received:2014-04-24 Revised:2014-05-20 Online:2014-11-25 Published:2014-07-02
  • Supported by:

    Project supported by the Promotive Research Fund for Excellent Young and Middle-aged Scientists of Shandong Province (No.BS2011NY013), the Innovation Fund for the Youth of Shandong Agricultural University (No.23682), the National Natural Science Foundation of China (No.21102173), the Project of Development of Science and Technology of Shandong Province (No.2013GZX20109) and the President Science Foundation of South China Agricultural University (No.4200-K13014).

为了寻找新型高效、低毒、环境友好的农药先导化合物, 以取代苯甲酸、α-甲氧基乙酸甲酯和甲酸乙酯为起始原料, 设计合成了22个未见报道的N-取代苯甲酰-N'-(5-甲氧基-2-甲硫基嘧啶-4-胺基)(硫)脲10a~10v, 其结构经1H NMR, IR和元素分析表征和确认. 对目标化合物进行初步杀菌活性和昆虫生长调节活性筛选, 生测结果表明: 部分化合物具有较好的杀菌活性, 如化合物10m10p在50 mg/mL下对黄瓜灰霉菌和油菜菌核菌的抑制率均超过70%, 其中对后者的抑制率高于对照药剂95%百菌清; 一些化合物对2~3龄库蚊幼虫表现出优良的昆虫生长调节活性, 化合物10o10r对幼虫的未羽化率达97.8%, 化合物10t对幼虫具有100%灭杀活性.

关键词: 苯甲酰脲, 嘧啶, 几丁质, 杀菌活性, 昆虫生长调节活性

In order to find new lead compounds with high effciency, low toxicity and environmental-friendly contribution, a series of novel N-(substituted benzoyl)-N'-(5-methoxyl-2-methylsulfanylpyrimidin-4-amino)(thio) ureas were designed and synthesized from substituted benzoic acids, α-methoxyl methyl acetate and ethyl formate. Their structures were confirmed by 1H NMR, IR and elemental analysis. The preliminary bioassay results indicated that some compounds exhibited considerate fungicidal activity. Among them compounds 10m and 10p showed more than 70% inhibitory rate to Botrytis cinerea and Sclerotinia sclerotiorum at 50 mg/mL, and the inhibitory rate against Sclerotinia sclerotiorum was higher than the control fungicide 95% chlorothalonil. Some compounds showed obvious insect growth regulation activity against 2~3 instar Culex larvae, compounds 10o and 10r showed 97.8% revised uneclosion rate, and compound 10t exhibited 100% insecticidal activity.

Key words: benzoylurea, pyrimidine, chitin, fungicidal activity, insect growth regulation activity